5 Tips for Living with the Uncertainty of a Startup

By Kristen Cooper, CEO & Founder, The Startup Ladies

Investors will pressure you to mitigate risk in every aspect of your business.  You control for as many variables as possible, but how do you live with so many unknowns?  

Normalizing uncertainty will not only help you succeed with your startup, it will help you become more of yourself and allow you to be fully present with your family, friends, and colleagues.  The following practices will help you develop confidence, deepen relationships with influencers, and get you through those tough times when you don’t have a crystal ball to predict the outcomes in your future.

Tip #1 - Develop healthy boundaries.

 You will be tempted to think about your startup every minute that you are conscious. One second you’re eating a bowl of Cornflakes, and the next second, you’re staring at that rooster on the cereal box thinking, “That’s a weird looking rooster.  Its eyes are so empty. What do our customers think about our logo? I need to talk to our marketing person. I wonder if we should collect some feedback about this?” And down the rabbit hole you go. To prevent yourself from relating everything to business, you will need to occupy your mind with both pleasurable and challenging quests, curiosities, and experiences. Otherwise, you will burn out, or worse yet, become the dullard at a party.

Engaging in activity that requires 100% of the brain’s focus will give you the cerebral break that you need while allowing you to absorb new concepts.  One of the best distractions I have experienced was taking a color value class in acrylics at a local art school. Mixing color to match a color is not easy.  In fact, sometimes creating a new color is controversial. I once spent two hours with my favorite artist, Rebecca Allan, trying to re-create a shade of pink she found in a painting.  She can look at any color palette and know exactly how to blend multiple colors to make an entirely new color.  This one art lesson has been the source of dozens of very satisfying conversations about understanding and making art.  The experience allowed me to connect with new influential people and be conversant in an area that is genuinely interesting.

Tip #2 - Put together a personal board of advisors.

When I ask founders if they have a personal board of advisors, nine times out of ten, they don’t have one.  It’s easy to put together. First, make a list of all the areas where you are not an expert and need to grow.  You don’t necessarily need someone who is a master of a trade. You need a teacher who is more experienced than you to be your sounding board. If you are not connected to an expert in a particular field, then attend Meetups and events where the experts go to learn and connect.  If you need someone at the very top of their game to advise you, read my article on how to win meetings with executives in the C-suite.

Tip #3 - Normalize failure.

Every one of us gets a sales “no,” underwhelms a customer, or loses a deal on occasion.  Losing never feels good. The anxiety caused by the fear of failure is often greater than the failure itself.  Next time you fail, just feel the pain for a few minutes. Then start to classify your failure. I learned this technique from Michael Cloran about five years ago. It completely changed how I interpret failure.  While you may have lost the deal, the process may have allowed you to gain a major insight that helps you in the future. When the failure is more significant, it’s time to reach out to your network. As you share your story of loss with the people who care for you most, you become a wiser, stronger, more empathetic you.  That’s winning.

Tip #4 - Normalize success.

 Ever experience some form of success that is quickly followed by pangs of anxiety?  Colleagues are toasting to your achievement, yet for some reason, you feel uneasy -- like the other shoe is about to drop. Instead of fearing what could possibly go wrong, re-contextualize and look forward to what might happen in the best possible way.  Sometimes it’s harder to visualize winning because winning comes with additional responsibilities. 

When you are clear about what the definition of success is, you create a healthy boundary and give yourself permission to pause and enjoy what you have accomplished. Establishing multiple opportunities for victory allows you to acknowledge and appreciate the moment of completion before moving on to the next challenge.  Purposefully recognizing what you and your team accomplished when a goal is achieved provides a reference point of competence and camaraderie. This is an easy and genuine method to build trust amongst team members.

Tip #5 - Work with a therapist - regularly.

CEOs who understand human behavior are concerned about creating corporate cultures where employees get to be themselves every day - all day long. In order to create a space that is safe for others, it’s important to understand yourself and how you are understood by others.Did you know that one-in-five adults experience some form of mental illness each year? Two of the most common forms of mental illness are depression and anxiety. Honestly, what founder doesn’t deal with bouts of depression and/or anxiety?  Only 41% of adults in the U.S. with a mental health condition received mental health services in the past year.  We get a sinus infection and we run to the doctor for some amoxicillin. Yet, we tolerate immeasurable suffering of the mind.  Think of all of the people (possibly you) who experience depression, anxiety, or some other form of mental illness and they don’t receive treatment. How can you expect to perform at your peak and be a rock for others when one of the most important organs in your body needs attention and care?

If you don’t take care of your mind and the minds of those you love, be aware that mental illness costs America $193.2 billion in lost earnings per year (National Alliance on Mental Illness - https://www.nami.org).  We need founders and funders to help destigmatize mental illness by understanding the problem and the vocabulary, and encouraging those around us to get the support they need to heal.  

You don’t need to be in the midst of a crisis to speak with a psychologist. Checking in with your therapist at least once a month will allow you to vent and learn how to better understand yourself and the behavior of those around you.  To find a therapist in your community, visit Psychology Today.

Uncertainty is manageable, but to do so, you have to surround yourself with trustworthy people who enable you to develop greater trust in yourself. If you want to be part of a community that supports founders, check out The Startup Ladies website. We’ve got events in Indianapolis, Terre Haute and Bloomington, Indiana.

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